Alkaloids fagaronine (I), dihydrofagaronine (XXV) and oxyfagaronine (XXVI) were synthesized from 2,3-dihydroxynaphthalene (II) and 2-bromo-4,5-dimethoxybenzaldehyde (XI), the key synthetic steps being the preparation of 2-hydroxy-3-methoxy-5-nitronaphthalene (VI) by partial methylation of 2,3-dihydroxy-5-nitronaphthalene (V) and formation of benzo[c]phenanthridone XXI by photocyclization of amide XVI.
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Jan Šmidrkal (1988) studied this question.
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